Holiday rentals in Winter Park

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Top-rated holiday rentals in Winter Park

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Flat in Winter Park
Get a Little Glam in a Retro Palm Beach-Style Boudoir
The whole upstairs portion of the building is all yours. Location is prime as it is close to all things wonderful in Winter Park FL. Two streets behind is Lake Killarney. The space is beautifully decorated and offers guests a charming get away. Please note: It is a 13.6 mile drive (21 - 40 minutes depending on traffic) from Universal Studio's and a 21.7mile drive (24 - 45 minutes depending on traffic) to Disney World. There is a lock box located under the stairwell on the left side of the building. I will message you with your code for access. Once you get your key, head on up the stairs and enjoy your home away from home. Welcome! I live 3 minutes away from the Air BnB property and I work in the downstairs portion of the building, so I am local and available to assist with any additional requests. Message me anytime! Or text 407 575 3502 The Fairbanks corridor of Winter Park is the main artery to affluent areas, offering great shopping and dining close by. This hidden gem is a short walk to grocery stores, restaurants, and Winter Park Village shopping district with its movie theater. Light sleepers, please be aware that there is the potential for traffic noise. The BnB offers a large parking lot. You should have no problem at all if you desire to arrive by car. The area is also safe to bike around and Uber or Lyft operates in the area. No smoking please.
22–29 Dec
₹8,286 per night
4.95 out of 5 average rating, 280 reviews
Guest favourite
Townhouse in Winter Park
Beautiful Downtown Winter Park
WP requires rentals to be listed as 28 days. For alternate rentals please contact me with dates requested. A 1 bedroom New England style townhouse. Enjoy brick streets, old oaks and lake access all within a 5 minute walk to downtown Winter Park, home of nationally known art festivals and museums, Saturday farmers market, Rollins College and many fine dining establishments. Pick herbs from our garden to use in cooking. Lounge on your private deck to the relaxing waterfall sounds of our koi pond.
15–22 Jun
₹9,058 per night
4.98 out of 5 average rating, 193 reviews
Guest favourite
Bungalow in Winter Park
Cozy 2/2 Bungalow - Downtown Winterpark/Orlando
Your family will be close to everything when you stay at this centrally-located bungalow. Located right off I-4, you will be 5 minutes from Downtown Orlando and Downtown Edgewater, 10 min from Downtown Winter Park, 15 min from Universal Studios, and 25 min from Disney! College Park local parks and golf course within walking distance! Large 70 inch 4K tv with surround sound, large sofa to enjoy watching your favorite movies, 2 rooms with queen beds, and 2 bathrooms equipped with bluetooth music
24–31 Jul
₹10,802 per night
4.98 out of 5 average rating, 222 reviews

Popular amenities for Winter Park holiday rentals

Stay near Winter Park's top sights

Orlando Science Center289 locals recommend
Winter Park Village68 locals recommend
Harry P. Leu Gardens197 locals recommend
AdventHealth Orlando25 locals recommend
Trader Joe's74 locals recommend
Mead Botanical Garden52 locals recommend

Other great holiday rentals in Winter Park

Guest favourite
Guest suite in Orlando
Private Fireplace Studio with contactless check in
17–24 Apr
₹6,735 per night
4.92 out of 5 average rating, 108 reviews
Guest favourite
Flat in College Park
Quiet Shed in Downtown
12–19 Feb
₹8,551 per night
4.95 out of 5 average rating, 613 reviews
Guest favourite
Guest house in Maitland
Private 1-bd Mid-Century Guesthouse
26 Jul – 2 Aug
₹7,201 per night
4.98 out of 5 average rating, 114 reviews
Superhost
Villa in Winter Park
Luxury Villa, 3bed/2bath Great Location with Pool
20–27 Nov
₹12,856 per night
4.83 out of 5 average rating, 103 reviews
Guest favourite
Guest house in Orlando
The Loft in College Park
21–28 Apr
₹6,332 per night
4.98 out of 5 average rating, 139 reviews
Guest favourite
Guest house in Orlando
Private Backyard Cottage in Mills50
15–22 Aug
₹6,814 per night
4.92 out of 5 average rating, 157 reviews
Superhost
Apartment in Winter Park
Lovely Winter Park Home close to Hospitals !
9–16 Nov
₹7,462 per night
4.81 out of 5 average rating, 54 reviews
Guest favourite
Flat in Winter Park
The Lake House
8–15 Dec
₹6,455 per night
4.88 out of 5 average rating, 25 reviews
Guest favourite
Apartment in Winter Park
Walk to Park Ave & The WP Village!
₹21,556 per night
4.94 out of 5 average rating, 35 reviews
Guest favourite
Bungalow in Winter Park
Charming Farmhouse Bungalow
10–17 Jun
₹8,954 per night
4.87 out of 5 average rating, 62 reviews
Guest favourite
Tiny home in Winter Park
Comfy Tiny Home @WP. Large Private Deck+Queen bed
4–11 Jul
₹10,372 per night
4.88 out of 5 average rating, 17 reviews
Guest favourite
Guest house in College Park
Amazing place in exclusive area Downtown Orlando
6–13 Dec
₹7,663 per night
4.93 out of 5 average rating, 44 reviews

Quick stats about holiday rentals in Winter Park

Total rentals

410 properties

Rentals with dedicated workspaces

240 properties have a dedicated workspace

Rentals with a pool

100 properties have a pool

Pet-friendly rentals

140 properties allow pets

Family-friendly rentals

200 properties are a good fit for families

Total number of reviews

17T reviews

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Orange County
  5. Winter Park